ethyl 2-[(2-methylanilino)methylidene]-3-oxohexanoate | 115607-94-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-[(2-methylanilino)methylidene]-3-oxohexanoate
• CAS: 115607-94-8
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: DLUUTDSNBGZXQW-UHFFFAOYSA-N

物化性质

• 沸点：
  382.6±42.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(2-methylanilino)methylidene]-3-oxohexanoate 在 三氯氧磷 作用下， 以 1,4-二氧六环 、 二苯醚 为溶剂， 反应 18.25h， 生成 3-butyryl-4-(2-methoxyphenylamino)-8-methylquinoline
  参考文献：
  名称：

  Reversible Inhibitors of the Gastric (H+/K+)-ATPase. 4. Identification of an Inhibitor with an Intermediate Duration of Action

  摘要：

  3-Acyl-4-(arylamino)quinolines were previously identified as gastric (H+/K+)-ATPase inhibitors, and clinical efficacy has been demonstrated for compound 3 (SK&F 96067). In the present study the further structure-activity relationship of this series is developed. Only a limited range of substituents are tolerated on the N-aryl ring or the 6- and 7-positions of the quinoline, and although hydroxylated derivatives were identified possessing markedly greater affinity for the enzyme, none of these proved to have adequate potency after oral dosing. In contrast, the 8-position of the quinoline ring proved suitable for a wide variety of substituents, allowing modification of physicochemical properties while retaining primary activity. This led to the identification of compound 4 (SK&F 97574), which combines good oral potency with a somewhat longer duration of action than 3 (though much shorter than covalent inhibitors such as omeprazole). This compound was selected for further development and evaluation in man.

  DOI：

  10.1021/jm00014a026
• 作为产物：
  描述：

  丁酰乙酸乙酯 在 乙酸酐 作用下， 反应 0.5h， 生成 ethyl 2-[(2-methylanilino)methylidene]-3-oxohexanoate
  参考文献：
  名称：

  Reversible Inhibitors of the Gastric (H+/K+)-ATPase. 4. Identification of an Inhibitor with an Intermediate Duration of Action

  摘要：

  3-Acyl-4-(arylamino)quinolines were previously identified as gastric (H+/K+)-ATPase inhibitors, and clinical efficacy has been demonstrated for compound 3 (SK&F 96067). In the present study the further structure-activity relationship of this series is developed. Only a limited range of substituents are tolerated on the N-aryl ring or the 6- and 7-positions of the quinoline, and although hydroxylated derivatives were identified possessing markedly greater affinity for the enzyme, none of these proved to have adequate potency after oral dosing. In contrast, the 8-position of the quinoline ring proved suitable for a wide variety of substituents, allowing modification of physicochemical properties while retaining primary activity. This led to the identification of compound 4 (SK&F 97574), which combines good oral potency with a somewhat longer duration of action than 3 (though much shorter than covalent inhibitors such as omeprazole). This compound was selected for further development and evaluation in man.

  DOI：

  10.1021/jm00014a026

文献信息

• 4-amino-3-carbonyl substituted quinolines
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04806549A1

  公开（公告）日：1989-02-21

  This invention relates to novel substituted 4-aminoquinoline derivatives which are inhibitors of gastric acid secretion in mammals. A compound of the invention is 3-butyryl-4-(2-methylphenylamino)-8-methoxyquinoline.

  本发明涉及一种新型的取代的4-氨基喹啉衍生物，其为哺乳动物胃酸分泌抑制剂。该发明的化合物为3-丁酰基-4-(2-甲基苯胺基)-8-甲氧基喹啉。
• 4-Amino-3-carbonyl substituted quinolines as inhibitors of gastric acid
  申请人：SmithKline & French Laboratories Limited

  公开号：US04806550A1

  公开（公告）日：1989-02-21

  This invention relates to novel substituted 4-aminoquinoline derivatives which are inhibitors of gastric acid secretion in mammals. A compound of the invention is 3-butyryl-4-(2-methylphenylamino)-8-methoxyquinoline.

  本发明涉及一种新型的取代的4-氨基喹啉衍生物，该衍生物是哺乳动物胃酸分泌抑制剂。本发明的一种化合物是3-丁酰基-4-(2-甲基苯胺基)-8-甲氧基喹啉。